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Spectroscopic investigation of interaction of 6-methoxyflavanone and its β-cyclodextrin inclusion complex with calf thymus DNA

Sameena Yousuf and Israel V. M. V. Enoch

Department of Chemistry, School of Science and Humanities, Karunya University, Coimbatore, 641 114 India

 

E-mail: israelenoch@karunya.edu

Abstract: The interaction of 6-methoxyflavanone (6MF, 6-methoxy-2-phenyl-4H-1-benzopyran-4-one) with calf thymus DNA (ctDNA) was investigated by absorption spectroscopy, fluorescence spectroscopy, and cyclic voltammetry in the presence and absence of β-cyclodextrin (β-CD) acting as capping agent. Molecular modelling was used to optimise the study of 6MF-β-CD and 6MF-DNA interactions. Enhancement in the fluorescence intensity of 6MF was observed due to the formation of 1 : 1 complex with β-CD. In the presence and absence of DNA, 6MF showed different characteristics such as hyperchromic effect, red shift of absorption spectra and fluorescence quenching of 6MF due to binding between 6MF and ctDNA. The nature of the binding group was found to be different for the 6MF-ctDNA and 6MF-ctDNA-β-CD systems. An increase in fluorescence intensity was observed for the 6MF-ctDNA system while varying the concentration of β-CD due to encapsulation of a part of 6MF in cyclodextrin. The results are compatible with the possibility of the interaction of dihydrobenzopyran-4-one moiety of 6MF with ctDNA as well as with β-CD. Cyclic voltammetric studies confirmed the binding interaction between 6MF and ctDNA in the absence and presence of β-CD and molecular modelling explains the site of the interaction of 6MF with cyclodextrin and ctDNA.

Keywords: 6-methoxyflavanone – β-cyclodextrin – ctDNA – fluorescence quenching

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-012-0180-0

 

Chemical Papers 66 (8) 787–794 (2012)

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